US4978614A - Method of detecting a substance using enzymatically-induced decomposition of dioxetanes - Google Patents
Method of detecting a substance using enzymatically-induced decomposition of dioxetanes Download PDFInfo
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- US4978614A US4978614A US07/382,125 US38212589A US4978614A US 4978614 A US4978614 A US 4978614A US 38212589 A US38212589 A US 38212589A US 4978614 A US4978614 A US 4978614A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
- G01N33/76—Human chorionic gonadotropin including luteinising hormone, follicle stimulating hormone, thyroid stimulating hormone or their receptors
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6816—Hybridisation assays characterised by the detection means
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/535—Production of labelled immunochemicals with enzyme label or co-enzymes, co-factors, enzyme inhibitors or enzyme substrates
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/581—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with enzyme label (including co-enzymes, co-factors, enzyme inhibitors or substrates)
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
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- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
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- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
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- General Physics & Mathematics (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Endocrinology (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
Description
TABLE 1 __________________________________________________________________________ Group Z Enzyme __________________________________________________________________________ (1) ##STR3## alkaline and acid phosphatases (2) ##STR4## esterases (3) ##STR5## decarboxylases (4) ##STR6## phospholipase D (5) ##STR7## β-xylosidase (6) ##STR8## β-D-fucosidase (7) ##STR9## thioglucosidase (8) ##STR10## β-D-galactosidase (9) ##STR11## α-D-galactosidase (10) ##STR12## α-D-glucosidase (11) ##STR13## β-D-glucosidase (12) ##STR14## α-D-mannosidase (13) ##STR15## β-D-mannosidase (14) ##STR16## β-D-fructofuranosidase (15) ##STR17## β-D-glucosiduronase (16) ##STR18## trypsin (17) ##STR19## trypsin __________________________________________________________________________
______________________________________ For Colorimetric Assay Chemiluminescence ______________________________________ 7. N/A 7. Washed once with 0.05M carbonate, 1 mM MgCl.sub.2 pH 9.5. 8. Added 200μl 1 mg/ml 8. Added 250 μl of 0.4 mM p-nitrophenyl-phosphate AMPPD in 0.05M carbonate, (PNPP) in 0.1M glycine, 1 mM MgCl.sub.2, pH 9.5 1 mM MgCl.sub.2, pH 10.4 9. Incubated for 30 minutes 9. Incubated for 20 minutes at room temperature at 30° C. 10. Added 11.5 ml of 0.1M 10. N/A glycine, 10 mM of EDTA, pH 9.5, to stop color development 11. Read absorbance at 405 11. Read 10 sec. integral of nm in spectrophotometer luminescence from each tube in Turner 20E Luminometer ______________________________________
TABLE II ______________________________________ Concentration of Alkaline Minimum Detectable Phosphatase for 2X Conc. of Alkaline Addition Background Phosphatase ______________________________________ None 1.0 × 10.sup.-14 1.67 × 10.sup.-15 M (1.12) ______________________________________ 1. Buffer: 0.05 M sodium carbonate, 1 mM MgCl.sup.2, pH 9.5. Temperature: 30° C. AMPPD concentration was 0.4 mM. 2. The number in parentheses is the multiple of background at the indicated concentration.
TABLE III ______________________________________ Concentration of Alkaline Minimum Detectable Phosphatase for 2X Conc. of Alkaline Addition Background Phosphatase ______________________________________ None 1.0 × 10.sup.-14 .sup. 1.67 × 10.sup.-15 M (1.12).sup.1 0.1% BSA 9.5 × 10.sup.-15 M 8.34 × 10.sup.-16 M (1.06) 0.1% BSA: 1.3 × 10.sup.-15 M 4.17 × 10.sup.-16 M (1.04) Fluorescein 0.1% BDMQ 4.0 × 10.sup.-15 M 1.00 × 10.sup.-16 M (1.07) 0.1% BDMQ: 3.4 × 10.sup.-15 M 2.09 × 10.sup.-16 M (1.06) Fluorescein ______________________________________ .sup.1 The number in parentheses is the multiple of background at the indicated concentration.
______________________________________ Final Concentration ______________________________________ 0.5ml 100 × Denhardt's 5% solution 0.5ml 10% SDS 0.5% 2.5ml 20 ×SSPE 5% 2.0 mg denatured, 200μg/ml sonicated salmon sperm DNA ddH.sub.2O 10 ml ______________________________________ Final Membrane Hybridization Buffer: Concentration ______________________________________ 0.5ml 100 × Denhardt's 5% solution 0.5ml 10% SDS 0.5% 2.5ml 20 ×SSPE 5% 2.0 mg salmon sperm DNA 200μg/ml 2.0ml 50% Dextran sulfate 10% ddH.sub.2O 10 ml Wash Buffer I: 1 × SSPE/0.1% SDS 20ml 20 ×SSPE 4ml 10% SDS 376 ml ddH.sub.2 O 400 ml Wash Buffer II: 0.1 × SSPE/0.1% SDS preheated to wash temperature. 2ml 20 ×SSPE 4ml 10% SDS 394 ml ddH.sub.2 O 400 ml (heated Wash Buffer III: 0.1 × SSPE/0.1% SDS 20ml 20 ×SSPE 4ml 10% SDS 394 ml ddH.sub.2 O 400 ml Wash Buffer IV: 3 mM Tris-HCl (pH 9.5) 0.6 ml IM Trizma Base 199.4 ml ddH.sub.2 O 200.0 ml ______________________________________
______________________________________ 20X SSC 20X SSC (for 100 ml) 3.0M Sodium Chloride 17.4 g 0.3M Sodium Citrate 8.8 g Bring volume to 100 ml and filter through a 0.45 μm nitrocellulose filter. Store at room temperature. 20X SSPE 20X SSPE pH 7.4 (for 1 liter) 3.6M NaCl 210.24g 200 mM Sodium phosphate 23 g dibasic 5.92 g monobasic 20 mM EDTA 7.44 g Dissolve, adjust pH to 7.4 with 5 N NaOH Bring volume to 1 liter and filter through a 0.45 μm nitrocellulose filter. 1X TE1X TE buffer 10 MM Tris (pH 7.0) 1 mM EDTA Autoclave ______________________________________
TABLE IV ______________________________________ Comparison of Detection Limits for Hepatitis B "Core Antigen" Plasmid DNA Using Chemiluminescent and Chromogenic Substrates in SNAP ® Hybridization Kit Chemiluminescent AMPPD Colorimeric Copies of BHS.sub.c Substrate BCIP/NBT Substrates DNA Per Spot Detection in Minutes Detection in Minutes ______________________________________ 9.8 × 10.sup.7 30 30 3.2 × 10.sup.7 30 60 1.07 × 10.sup.7 30 120 3.56 × 10.sup.6 30 180 1.18 × 10.sup.6 30 240 3.95 × 10.sup.5 60 no color 1.31 × 10.sup.5 90 no color 4.39 × 10.sup.4 120 no color ______________________________________
______________________________________ For Colorimetric Assay Chemiluminescence ______________________________________ 9. N/A 9. Washed 1 time with 0.5M carbonate, 1 mM MgCl.sub.2 pH 9.5. 10. Added 200 μl of 1 mg/ml 10. Added 250 μ of 0.4 mM p-nitrophenyl-phosphate AMPPD in 0.05M in 0.1 (PNPP)glycine 1 mM carbonate, 1 mM MgCl.sub.2 pH MgCl.sub.2 pH 10.4 9.5. 11. Incubated for 30 minutes 11. Incubated for 20 minutes at room temperature at 30° C. 12. Added 1.5 ml of 0.1 M 12. N/A glycine, 10 mM EDTA, pH 9.5 to stop color development 13. Read in absorbance at 410 13. Read 10 sec. integral of nm in spectrophotometer each tube in Turner luminometer ______________________________________
TABLE V ______________________________________ TSH Concentration (μU/ml) (Counts/10 sec × 10.sup.-4) ______________________________________ 1 0.25 2 0.49 4 1.1 ______________________________________
______________________________________ Tube # Conc. hLH in ng/ml of PBS ______________________________________ 1 0 2 1 3 10 4 100 ______________________________________
______________________________________ Reaction Mixtures (Nanograms of Nucleotides) G A T C ______________________________________ Deoxynucleotides dGTP 1022.9 1077.4 1102.9 1102.9 dCTP 1015.9 992.4 1015.9 942.9 dTTP 1048.6 1048.6 972.5 1048.6 dATP 985.5 985.5 985.5 985.5 Dideoxynucleotides ddGTP 123.0 -- -- -- ddCTP -- 29.7 -- -- ddTTP -- -- 466.0 -- ddATP -- -- -- 113.0 ______________________________________
TABLE VI ______________________________________ Oligonucleotide, Earliest Detection Time, Sec. ng Nylon Nitrocellulose PVDF ______________________________________ 200 1 60 * 67 1 60 * 22 1 300 * 7.4 1 300 * 2.5 1 300 * 0.82 1 * * 0.27 1 * * 0.091 10 * * 0.03 60 * * 0.01 60 * * ______________________________________ *Not detectable by 10 min. of exposure.
Claims (66)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/382,125 US4978614A (en) | 1988-10-26 | 1989-07-20 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
CA002033331A CA2033331C (en) | 1989-07-20 | 1990-07-17 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
EP98122597A EP0907082A3 (en) | 1989-07-20 | 1990-07-17 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
EP98101157A EP0859062A3 (en) | 1989-07-20 | 1990-07-17 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
EP90911242A EP0435998B1 (en) | 1989-07-20 | 1990-07-17 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
PCT/US1990/003920 WO1991001492A1 (en) | 1989-07-20 | 1990-07-17 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
DE69033347T DE69033347T2 (en) | 1989-07-20 | 1990-07-17 | METHOD FOR DETECTING A SUBSTANCE USING THE ENZYMATIC DEGRADATION OF DIOXETANES |
US07/574,787 US5220005A (en) | 1986-07-24 | 1990-08-30 | Substituted adamantyl dioxetanes |
US08/255,795 US5605795A (en) | 1986-07-24 | 1994-06-07 | Assays using chemiluminescent, enzymatically cleavable substituted 1,2-dioxetanes and kits therefor |
US08/958,342 USRE36536E (en) | 1986-07-24 | 1997-10-27 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26540688A | 1988-10-26 | 1988-10-26 | |
US07/382,125 US4978614A (en) | 1988-10-26 | 1989-07-20 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US26540688A Continuation-In-Part | 1986-07-24 | 1988-10-26 | |
US07/265,405 Continuation-In-Part US4968583A (en) | 1987-10-31 | 1988-10-31 | Pattern forming method employing electron beam lithography |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/574,787 Continuation-In-Part US5220005A (en) | 1986-07-24 | 1990-08-30 | Substituted adamantyl dioxetanes |
US08/958,342 Reissue USRE36536E (en) | 1986-07-24 | 1997-10-27 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
Publications (1)
Publication Number | Publication Date |
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US4978614A true US4978614A (en) | 1990-12-18 |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/382,125 Expired - Lifetime US4978614A (en) | 1986-07-24 | 1989-07-20 | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
Country Status (4)
Country | Link |
---|---|
US (1) | US4978614A (en) |
EP (3) | EP0907082A3 (en) |
DE (1) | DE69033347T2 (en) |
WO (1) | WO1991001492A1 (en) |
Cited By (64)
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US5145772A (en) * | 1986-07-24 | 1992-09-08 | Tropix, Inc. | Chemiluminescence enhancement of enzyme-activated decomposition of enzymatically cleavable chemiluminescent 1,2-dioxetanes |
WO1992021778A1 (en) * | 1991-06-05 | 1992-12-10 | Life Technologies, Inc. | Assays employing anchimeric assistance cleavage |
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US5206136A (en) * | 1986-11-19 | 1993-04-27 | Genetic Systems Corporation | Rapid membrane affinity concentration assays |
US5220005A (en) * | 1986-07-24 | 1993-06-15 | Tropix, Inc. | Substituted adamantyl dioxetanes |
US5223402A (en) * | 1990-08-30 | 1993-06-29 | Difco Laboratories | Method of detecting microbes utilizing chemiluminescent compound |
WO1993013405A1 (en) * | 1991-12-23 | 1993-07-08 | Tropix, Inc. | Improved membrane for chemiluminescent blotting applications |
US5241070A (en) * | 1988-09-26 | 1993-08-31 | Ciba Corning Diagnostics Corp. | Nucleophilic polysubstituted aryl acridinium esters and uses thereof |
EP0561033A1 (en) * | 1992-03-20 | 1993-09-22 | Lumigen, Inc. | Polymeric phoshonium salts providng enhanced chemiluminescence from 1,2-dioxetanes |
US5320944A (en) * | 1989-09-29 | 1994-06-14 | Fujirebio Inc. | Immunoassay using magnetic particle |
US5330900A (en) * | 1987-12-31 | 1994-07-19 | Tropix, Inc. | Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes |
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US5340716A (en) * | 1991-06-20 | 1994-08-23 | Snytex (U.S.A.) Inc. | Assay method utilizing photoactivated chemiluminescent label |
US5342760A (en) * | 1992-06-10 | 1994-08-30 | Abbott Laboratories | Determination of estradiol by competitive immunoassay |
US5385823A (en) * | 1991-12-27 | 1995-01-31 | Aisin Seiki Kabushiki Kaisha | Method for assaying nucleic acids and proteins using anthracene derivative phosphate |
US5441894A (en) * | 1993-04-30 | 1995-08-15 | Abbott Laboratories | Device containing a light absorbing element for automated chemiluminescent immunoassays |
US5449556A (en) * | 1988-08-01 | 1995-09-12 | Ciba Corning Diagnostics Corp. | Method for detection of an analyte using acridinium esters and liposomes |
US5451347A (en) * | 1993-06-24 | 1995-09-19 | Lumigen, Inc. | Methods and compositions providing enhanced chemiluminescence from chemiluminescent compounds using dicationic surfactants |
US5591591A (en) * | 1995-02-09 | 1997-01-07 | Tropix, Inc. | Dioxetane compounds for the chemiluminescent detection of proteases, methods of use and kits therefore |
US5605795A (en) * | 1986-07-24 | 1997-02-25 | Tropix, Inc. | Assays using chemiluminescent, enzymatically cleavable substituted 1,2-dioxetanes and kits therefor |
US5618732A (en) * | 1992-07-31 | 1997-04-08 | Behringwerke Ag | Method of calibration with photoactivatable chemiluminescent matrices |
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US5663074A (en) * | 1988-09-26 | 1997-09-02 | Chiron Diagnostics Corporation | Nucleophilic polysubstituted aryl acridinium ester conjugates and syntheses thereof |
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Also Published As
Publication number | Publication date |
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EP0435998B1 (en) | 1999-11-10 |
EP0435998A4 (en) | 1993-03-10 |
DE69033347T2 (en) | 2000-06-15 |
EP0435998A1 (en) | 1991-07-10 |
EP0907082A2 (en) | 1999-04-07 |
EP0859062A3 (en) | 2006-01-25 |
EP0907082A3 (en) | 2005-12-14 |
WO1991001492A1 (en) | 1991-02-07 |
EP0859062A2 (en) | 1998-08-19 |
DE69033347D1 (en) | 1999-12-16 |
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